[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12](OC)=[O:13])=[CH:7][CH:6]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][OH:13])=[CH:7][CH:6]=2To a stirred solution of methyl 3-bromo-quinoline-6-carboxylate (1.09 g, 4 mmol) in THF (50 mL) at 0° C. was added LiAlH4 (0.155 g, 4 mmol) in small portions. The resulting mixture was stirred at 0° C. for 0.5 h. Water (0.2 mL) was added dropwise, followed by 0.2 mL of 10% aq. NaOH and 0.2 mL of water. The solid was removed and the solvent was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient to afford the title compound (413 mg, 42%). LCMS (method A): [MH]+=238/240, tR=4.453 min.
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